Jay, thanks for that very interesting Apple Support link. I read all the way through it and it gave me some ideas. But note that those posts all concerned people that were having trouble getting or sending mail through iCloud. I don't use and have no interest in mail through iCloud and my Olypen e-mail is working just fine. This error message about being unable to connect to the cloud is probably having some OTHER problem (that I'm not even aware of .....) but mail is not one of them.

I keep being totally frustrated both by the reappearing iCloud cannot connect problem AND the need to log in to each website with a password each time I visit it. (Although the password seems to stick sometimes for a few hours. But then after that... name and password must be entered once again).

Well yes... I log into websites on both my Mac and my iPhone. But the whole idea of an iCloud password or the iCloud's password in the Keychain are utterly baffling to me. Is there a troubleshooting procedure?

I'm not sure how iCloud keychain works but if I read this correctly it seems Safari and iCloud keychain might be fighting with each other when it comes to saved passwords. I'm wondering if turning off iCloud keychain might be one step in narrowing down the problem.http://support.apple.com/en-us/HT5813

Can I remove my iCloud Keychain from Apple's servers?
Yes. Use these steps on any of your iOS devices or Mac computers that are using iCloud Keychain:

Choose Apple () menu > System Preferences. Click iCloud, then click Account details.
Deselect “Allow approving using security code."
Go to each of your devices that are using iCloud Keychain and turn iCloud Keychain off.
After you complete these steps, your keychain data will remain locally on your devices, but changes to your keychain information won't push to your other devices or the cloud unless you turn iCloud Keychain back on. If you want keychain data to push to all of your devices, but not to the cloud, turn on iCloud Keychain on each device, but skip the step to create an iCloud Security Code.

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This is where I'd normally write an impressive summary of my skills and proficiencies.

I believe that iCloud Keychain is just a way to sync saved passwords among your Mac and iPhones and iPads.
Safari does have two methods of dealing with passwords.
One is Autofill. You can look at and manage the Autofill list.
The second is when you respond Yes to Safari's request to save a login. That info is saved to your Mac Keychain, which is managed in Keychain Access app.

If you sync Keychain, saved passwords should work in iOS as well as in OS X. (This also syncs information to fill in credit card information.) If I remember correctly, you need to have a password on your iOS device to use this feature.

I had a problem with Safari autofilling my Apple ID password when I log into Apple Support forums. It was using an outdated password. I finally got that fixed, but in a sort of shotgun approach of deleting anything Apple in Autofill and in Keychain.

Thanks Stephen and Jay for these most interesting websites. I will have to laboriously and time-consumingly wade through all of that information. You know... that stuff about conflicting keychains, iCloud preferences, etc. etc. etc. etc. is all too complicated, counter intuitive, and clumsy. It is a blot on Apple's engineering and good intentions. I dislike all of it. Mistrust it. And can easily understand why people would leave the whole pack of it in a second if another company offered an alternative way of doing things. The whole thing is dumbed down to the point where an ignoramus can use it by not touching any part of it or understanding any part of it. But if ANYTHING goes wrong... anything however slight.... then it is instantly too complex for ANYONE to understand it. Apple is a party to this poor design and because of that, has lost its Mojo. They are now no better or worse than dozens of other software companies.

After I had shown him my brand new Macintosh in 1984, a professor at my university came in to my office waving his sheet of DOS prompt commands in order to convince me that "it's possible to do all of those things you do on your Macintosh." He didn't understand that the new Macintosh had just done away with all of those memorized DOS commands forever.

I feel that this ridiculous complexity will all disappear instantly when the next great computer company figures out how to put elegance into motion. I love that quote that Steve Jobs always used.... attributed to Leonardo da Vinci that "simplicity is the ultimate sophistication."

I just don't get it. This isn't working. Have logged in and out of iCloud Keychain. Have logged in and out of iCloud. Have "Reset Safari" a number of times. Have checked the Safari settings panel that says "AutoFill User names and Passwords." All to no avail. Each time I visit a website I have to log in again. Each time, Keychain helpfully offers to fill in the username and password. Each time I click on the Keychain offered username and password I am instantly and correctly logged in. But why do I have to do this each and every time? Here is a screen shot showing the proffered Keychain login.

Have not methodically checked this with other browsers (Chrome and Firefox) but will do that now.

OK, here's another question for you. How does one download a clean new version of Safari 8.0.2 ? One would think that Apple's website would be of some help? Apparently not. They steal defeat from the jaws of victory.